.BETA.HYDROXYALKYLAMIDES, PROCESS FOR THEIR PRODUCTION AND THEIR USE

B-HYDROXYALKYLAMIDES, PROCEDE DE PRODUCTION ET UTILISATION

English Abstract

This invention relates to a .beta.-hydroxyalkylamide having the general Formula I: (see formula I) where R1 is H or a linear or branched C1 to C10 alkyl and R2 is a linear or branched C1 to C5 alkyl.

French Abstract

La présente invention a pour objet un .bêta.-hydroxyalkylamide de formule générale I (voir la formule I) dans laquelle R1 est H ou un alkyle en C1-C10 linéaire ou ramifié et R2 est un alkyle en C1-C5 linéaire ou ramifié.

Claims

7
The embodiments of the invention in which an exclusive property or
privilege is claimed are defined as follows:
1. A process for the production of a .beta.-hydroxyalkyl-amide having the
general
Formula I:
<IMG>
wherein R1 is H or a linear or branched C1 to C10 alkyl and R2 is a linear or
branched C1 to C5 alkyl;
wherein a carboxylic acid derivative having the general Formula II:
<IMG>
wherein R3 is halogen, is reacted with an alkanol amine having the general
Formula III:
<IMG>
2. The process as claimed in claim 1, wherein R1 is H, t-butyl, i-propyl or
pentyl and is located in the para position to the CO group.

8
3. The process as claimed in claim 2, wherein R1 is H and R2 is CH3.
4. The process as claimed in any one of claims 1 to 3, wherein the alkanol
amine having the general Formula III is reacted at -10 to 25 °C.
5. The process as claimed in any one of claims 1 to 4, wherein benzoyl
chloride is used as the carboxylic acid derivative and diisopropanol amine as
the
alkanol amine.
6. The process as claimed in any one of claims 1 to 5, wherein the carboxylic
acid derivative having the general Formula II and the alkanol amine having the
general Formula III are reacted in a solvent with vigorous agitation or
stirring.
7. The process as claimed in any one of claims 1 to 6, wherein at least one
aromatic hydrocarbon is used as the solvent.
8. The process as claimed in claim 7, wherein the aromatic hydrocarbon
comprises benzene, toluene, xylene or ether, or any combination thereof.
9. The process as claimed in any one of claims 1 to 8, wherein the alkanol
amine is presented first and the carboxylic acid derivative is added with
vigorous
agitation or stirring.

Description

CA 02359768 2001-10-23
1
EMS-Chemie AG
"Primid I{"
11 -Hydroxyatklyamides, process for their production and their use
This invention relates to novel f3-hydroxyalkylamides, a method for their
production and
their use.
f3-hydroxyalkylamides are very important as intermediate products and as cross
linkers
for polymers. &hyd roxya Ikyl am ides are conventionally produced by the
aminolysis of
alkyl esters with B-alkanol amines in the presence of basic catalysts. The f3-
hydroxyalkylamides are isolated and purified either, by crystallization in a
solvent or,
especially with solid 9-hydroxyalkylamides, without the use of solvent in a
slurry
process. A process of the above referenced type is described in US 5,101,073
and in
EP 0 473 380 B1. The slurry process is based on the fact that the equilibrium
reaction

CA 02359768 2008-10-29
2
that occurs during the production of the 13-hydroxyalkylamides is shifted
toward the
desired end product as a result of the fact that the desired f3-
hydroxyalkylamide is
precipitated from the melt by tempering in a defined temperature range and the
melt is
then crystallized. A disadvantage of this method is the use of equimolar
quantities of
alkyl ester and f1-hydroxyalkylamide.
An additional process for the production of f3-hydroxyalkylamides is described
in DE 198
23 925. In this method, the ester is converted without the use of solvents
with the
alkanol amines in the presence of basic catalysts.
EP-A-322 834 describes a powder coating which contains a polyester and (3-
hydroxyalkylkamides as cross linkers "(curing agents). Corresponding coatings
with
good characteristics can be produced with the formulation described in said
document.
On account of the major importance of (3-hydroxyalkylamides as an intermediate
product, especially as cross linkers for polyester powder coats as disclosed
in EP-A-322
834, there has recently been a great deal of interest in new and innovative (3-
hydroxyalkylamides.
On the basis of the prior art described above, an object of this invention is
to propose
new, previously unknown 9-hydroxyatkylamides and a corresponding process for
their
production.

CA 02359768 2008-10-29
3
The 9-hydroxyalkylamide claimed by the invention is defined by the general
Formula I
R2
Cx2 &-OH
A --N
Rl CHZ CH-QH
~Z2
z
In Formula 1, R, stands for hydrogen or a linear or branched Ci to Clo alkyl.
R2 is a
linear or branched Ci to C5 alkyl. The R-hydroxyalkylamides claimed by the
invention
are characterized in particular by the substituted carbon atom next to the OH
group. In
the (3-hydroxyalkylamides claimed by the invention, the R2 group is located
here.
The R-hydroxyalkylamide is preferably constructed so that the R, group is H,
tert-butyl,
isopropy{ or pentyl and is located in the para position to the CO group.
One particularly advantageous realization of the invention is characterized by
the fact
that the R, group is hydrogen and the R2 group is methyl.

CA 02359768 2001-10-23
4
These 9-hydroxyalkylarnides are produced by converting a carboxylic acid
derivative
having the general Formula II
O
ILR3
Iz
with an alkanol amine having the general Formula Ill.
R2
CH 2-- H--0H
HN
~CHZ--CH OH
2
IzZ
The Ri and R2 groups thereby have the definitions presented above. The R3
group can
thereby be a halogen, preferably chlorine, or an OR4 group. If there is an OR4
group, R4
is a linear C, to C5 alkyl, preferably a -CH3 group.

CA 02359768 2001-10-23
The conversion of the carboxylic acid derivative and the alkanol amine
preferably takes
place in a solution. Preferred solvents include but are not restricted to:
aromatic hydrocarbons such as benzene, toluene or xylene. Ethers such as
diethylether
.or mixtures of the solvents listed above are also suitable.
An essential feature of the process claimed by the invention is that the
carboxylic acid
derivative having the general Formula Il and the alkanol amine having the
general
Formula III are reacted with vigorous agitation of stirring. The alkanol amine
is thereby
preferably presented first and the carboxylic acid derivative is then added by
drops with
vigorous agitation of stirring.
For the case of the carboxylic acid halide, the conversion takes place at -10
to 25 C,
preferably at 0 to 10 C. The reaction time is normally 0.5 to 5 hours. A
reaction time of
2 hours is most advantageous.
If esters are included in the process (R3 = OR4), the reaction temperature at
RT is up to
150 C.
.
The 13-hydroxyalkylamide is particularly well suited as a cross linker for
polymers. f3-
hydroxyalkylamide is particularly preferred as a cross-linker for powder coats
with
polyesters or acrylates as the polymer.
Basically, the f3-hydroxyalkylamide can be used as a cross linker (curing
agent)
analogous to the 13-hydroxyalkylamides cited in EP-A-322 A34. The 13-
hydroxyaikyiamides taught by the invention can also be used in combination
with other
curing agents. One example of this usage is the curing agent sold under the
name
PRIMID by EMS-CHEMIE AG, Domat/Ems. PRIMID is N,N,N',N' 2-
hydroxyethyladipamide.

CA 02359768 2001-10-23
6
The invention is explained In greater detail below with reference to one
example of
production for the preferred embodiment of the invention, in which R, is H and
R2 is
CH3.
Production example:
44.16 g (0.32 mol) of non-aqueous K2CO3, 42.56 g (0.32 mol) of diisopropanol
amine,
160 ml of water and 160 ml of diethylether are placed in a 1-liter four-necked
round flask
with agitator, funnel, thermometer and reflux cooler. Using the funnel, 44.96
g (0.32
mol) of benzoyl chloride are added and dissolved in 160 ml toluene. This
solution is
then added in drops to the reaction flask over 2 hours with vigorous agitation
or stirring.
During the addition, the temperature of'the reaction mixture is held between 0
and 5 C.
After the addition, the agitation is continued for another 30 minutes at 0 to
5 C. Then
the ice bath is removed and the mixture is agitated or stii-red for another 50
minutes at
room temperature.
The precipitate that forms during the reaction is filtered out, washed twice
with 35 ml of
. toluene and then three times with 30 ml of diethyl ether and then dried at
50 C in a
vacuum. The dried raw product (74.28 g) is boiled in benzene (25% solution),
the
insoluble portions are filtered out and the product is crystallized at room
temperature.
After filtration and drying, 51.80 g (68%) of N,N-Bis-(2-hydroxyisopropyl)-
benzamide is
obtained with a melting point of 103 C. Elementary analysis: Calculated for
C13H19NO3:
C = 65.82%, H = 8.02%, N 5.91 %, 0 20.25%. Found: C 66.25%, H 8.09%, N
5.83%, 0 = 19.83%.

Representative Drawing